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Top 10 Best Hawaii Sailing Trips

Found 106 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 505 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb505 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 152 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Hawaii
  • Superb152 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

(4.9 of 204 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Free Cancellation
Start From $200.00
 
Molokini Snorkel and Performance Sail from Ma'alaea Harbor

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

  • Hawaii
  • Superb204 reviews4.9

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Start From $200.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 137 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb137 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 35 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb35 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 241 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb241 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 659 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Start From $178.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb659 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Start From $178.00
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(5 of 168 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb168 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

Waikiki Sunset Boat Cruise

(5 of 43 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb43 reviews5

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $50.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 728 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb728 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb147 reviews4.7

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Start From $79.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 261 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Free Cancellation
Start From $99.00
 
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb261 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Free Cancellation
    Start From $99.00
 
 

Sunset Cocktail Cruise from Anaeho'omalu Bay

(4.8 of 59 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Start From $165.00
 
Sunset Cocktail Cruise from Anaeho'omalu Bay

Sunset Cocktail Cruise from Anaeho'omalu Bay

  • Hawaii
  • Superb59 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Start From $165.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 923 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $89.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb923 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $89.99
 
 

Luxury Catamaran Whale Watch

(5 of 40 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Hawaii
  • Superb40 reviews5

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Start From $159.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 461 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb461 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 233 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Hawaii
  • Superb233 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Start From $49.99
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 108 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb108 reviews4.9

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Start From $125.00
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 37 reviews)

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More

Special Offer
Free Cancellation
Start From $99.96
(Saving 16% ) $119.00
 
-16% Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb37 reviews4.8

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....

    Special Offer
    Free Cancellation
    Start From $99.96
    (Saving 16% ) $119.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 800 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $149.00
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb800 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $149.00
 
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